Diisopropylethylamine → (R)-3-(6-Methoxy-pyridin-3-yl)-3-[6-(5-methyl-pyridin-2-yl)-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-4-ylamino]-propan-1-ol

HRID 241880Notes

Reaction equation

HRID 241880 reaction equation
Cl[C:2]1[C:3]2[CH2:11][N:10]([C:12]3[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][N:13]=3)[CH2:9][CH2:8][C:4]=2[N:5]=[CH:6][N:7]=1.[NH2:19][C@@H:20]([C:24]1[CH:25]=[N:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=1)[CH2:21][CH2:22][OH:23].C(N(CC)C(C)C)(C)C>C(#N)C>[CH3:31][O:30][C:27]1[N:26]=[CH:25][C:24]([C@H:20]([NH:19][C:2]2[C:3]3[CH2:11][N:10]([C:12]4[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][N:13]=4)[CH2:9][CH2:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH2:21][CH2:22][OH:23])=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 55264334(R)-3-amino-3-(6-methoxypyridin-3-yl)propan-1-olHCID 593464574-Chloro-5,6,7,8-tetrahydro-6-(5-methylpyridin-2-yl)pyrido[4,3-d]pyrimidine

Product 1

HCID 25032348(R)-3-(6-Methoxy-pyridin-3-yl)-3-[6-(5-methyl-pyridin-2-yl)-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-4-ylamino]-propan-1-ol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A reaction mixture of 4-chloro-5,6,7,8-tetrahydro-6-(5-methylpyridin-2-yl)pyrido[4,3-d]pyrimidine (45 mg, 0.17 mmol) and (R)-3-amino-3-(6-methoxypyridin-3-yl)propan-1-ol (31 mg, 0.17 mmol) (prepared similarly according to the method for Intermediate 10) in acetonitrile (2 mL) and N,N-diisopropylethylamine (60 μL, 0.34 mmol) was subjected to microwave irradiation at 180° C. for 1 h. The reaction mixture was concentrated and purified by semi-prep HPLC to give a light yellow foam.

Workup

  1. customprepared similarly
  2. customirradiation at 180° C. for 1 h
  3. concentrationThe reaction mixture was concentrated
  4. custompurified by semi-prep HPLC
  5. customto give a light yellow foam

Sources & evidence

ORD record
ord-c5b50b72e4e64bb5b388ea71eec5e712
Source dataset
uspto-grants-2014_02
Patent number
US08653091B2

Reaction notes

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